Table 7. Reaction of Ethyl Propiolate with Dodecanethiol Employing Different Organocatalysts at 0.1 M and Ambient Temperature76.
| catalyst | loading (mol %) | time (min) | conversion (%) | E/Z |
|---|---|---|---|---|
| n-hexylamine | 10 | 60 | 0 | |
| isopropylamine | 10 | 60 | 0 | |
| diisopropylamine | 10 | 60 | <1 | 50/50 |
| dicyclohexylamine | 10 | 60 | <1 | 50/50 |
| NEt3 | 10 | 60 | 85 | 97/3 |
| DIPEAa | 10 | 60 | <1 | 50/50 |
| DBUb | 1 | 10 | 100 | 34/66 |
| TBDc | 0.1 | 10 | 100 | 10/90 |
| PPhMe2 | 1 | 10 | 100 | 50/50 |
| PPh3 | 1 | 60 | 20 | 30/70 |
a
DIPEA = diisopropylethylamine.
b
DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene.
c
TBD = 1,5,7-triazabicyclo[4.4.0]dec-5-ene